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Meliaceous Limonoids: Chemistry and Biological Activities

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Meliaceous Limonoids: Chemistry and Biological Activities REVIEW pubs.acs.org/CR Meliaceous Limonoids: Chemistry and Biological Activities ‡ ‡ Qin-Gang Tan ,§ and Xiao-Dong Luo*, ‡ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650204, P.R.China §Guilin Medical University, Guilin, 541004, P.R.China CONTENTS 5.2.2. Antimicrobial Activity BR 1. Background and Introduction A 5.2.3. Antiprotozoal Activity BR 2. Meliaceous Limonoids and Their Sources E 5.2.4. Others BS Author Information BT 2.1. Ring Intact Limonoids E Biographies BT 2.1.1. Azadirone-Class E Acknowledgment BT 2.1.2. Cedrelone-Class F References BU 2.1.3. Havanensin-Class G 2.1.4. Trichilin-Class H 2.1.5. Vilasinin-Class H 1. BACKGROUND AND INTRODUCTION 2.1.6. Others I The word “limonoids” originated from the bitterness of lemon 2.2. Ring-seco Limonoids I or other citrus fruit. Structurally, limonoids are formed by loss of 2.2.1. Demolition of a Single Ring I four terminal carbons of the side chain in the apotirucallane or apoeuphane skeleton and then cyclized to form the 17β-furan 2.2.2. Demolition of Two Rings M ring, and thus limonoids are also known as tetranortriterpenoids. 2.2.3. Demolition of Three Rings (Rings Limonoids in the plant kingdom occur mainly in the Meliaceae A,B,D-seco Group) R and Rutaceae families and less frequently in the Cneoraceae.1 2.3. Rearranged Limonoids R With 50 genera and more than 1400 species, Meliaceae are distributed in tropical and subtropical regions throughout the 2.3.1. 1,n-Linkage Group R world.2 As the characteristic natural products of the Meliaceae, 2.3.2. 2,30-linkage Group T limonoids have attracted considerable interest within the chemi- 2.3.3. 8,11-Linkage Limonoids (Trijugin-Class) AA cal and biological research communities. The neem tree 2.3.4. 10,11-Linkage Limonoids (Azadirachta indica), one of the most famous limonoid produ- (Cipadesin-Class) AA cing plants in Meliaceae, has long been recognized as a source of environment-friendly biopesticide. Azadirachtin (292), a com- 2.3.5. Other Linkages Group AB plex limonoid from neem seed kernel, is the main component 2.4. Limonoids Derivatives AC responsible for the toxic effects on insects. The commercial 2.4.1. Pentanortriterpenoids, Hexanortriterpe- application of the limonoids in the agricultural industry has noids, Heptanortriterpenoids, Octanor- enjoyed significant growth in recent decades. Commercial neem triterpenoids, and Enneanortriterpenoids products (seed kernel extract of A. indica), such as Margosan-O, Azitin, Turplex, and Align were granted approval for pest control Derivatives AC À usage in the United States by the EPA.3 5 Furthermore, A. indica 2.4.2. Simple Degraded Derivatives AD was also introduced and has been planted on a large scale in 2.4.3. N-Containing Derivatives AD Yunnan province, P. R. China since the 2000s (Figure 1). Three 3. Chemotaxonomic Significance of Meliaceous commercial limonoids products (extracts of A. indica, Melia Limonoids AD toosendan, and M. azedarach), known as biorational insecticides, 4. Synthesis of Meliaceous Limonoids AF were also granted approval in China for insect control on organic 5. Biological Activities of Meliaceous Limonoids AV vegetable plantings. In a pharmaceutical application from China, a formulation with toosendanin, a limonoid from M. toosendan 5.1. Biological Activities in Agricultural Use AW that displays dramatic antibotulismic effects, was developed as a 5.1.1. Insects Antifeeding Activity AW commercial product from TCM (Traditional Chinese Medi- 5.1.2. Insects Growth Regulatory Activity BC cine), where it has been used as an anthelmintic vermifuge 5.1.3. Insecticidal Activity BL against ascarids for a long time.6 5.1.4. Antiphytopathogen Activity BM Some mini-reviews related to limonoids from Meliaceae have 7À13 5.1.5. Others BM been presented since 1966. For example, the chemistry, 5.2. Biological Activities in Medicinal Use BP Received: December 14, 2009 5.2.1. Antineoplastic Activity BP r XXXX American Chemical Society A dx.doi.org/10.1021/cr9004023 | Chem. Rev. XXXX, XXX, 000–000 Chemical Reviews REVIEW À À biosynthesis,1,13 15 and biological activities16 18 of meliaceous insect-growth-regulating activity,25,28,29 as well as its environ- limonoids were summarized in different years. It is noteworthy mental behavior,19 and its physiological behavior properties.30,31 that some reviews emphasize the well-known azadirachtin (292) In addition, the toxicity characteristics of azadirachtin and the À À and aspects of its chemistry,19 22 synthesis,23,24 and bioactivities mechanisms of its insecticidal action32 35 were also reviewed. À including antifeedant activity,25 27 insecticidal activity,25 and Reviews on the chemistry and biological activities of limo- À noids from Azadirachta indica,36 43 Melia azedarach, and À M. toosendan37,44 47 have been presented. Moreover, some other reviews related to meliaceous limonoids have also been pub- lished, such as those on the chemistry of cedrelone (81),48 the biological activity of gedunin (416),49 and the occurrence, biosynthesis, biological activity, and NMR spectroscopy of D and B,D-ring seco-limonoids from Meliaceae.50 However, none of them gave general insight into the chemistry and biological Figure 1. Azadirachta indica at Yuanmou county, Yunnan Province, activities of meliaceous limonoids. P. R. China. (A) Neem seedlings were bred on a large scale. (B) Neem trees During our investigations on the biologically active consti- were cultivated at both sides of the road. (C) Four-year-old neem trees tuents of Meliaceae, we noticed confusion and ambiguity about produced plenty of fruit. Photographs courtesy of Dr. Yanping Zhang. limonoids in the literature. (i) Some limonoids structures were Figure 2. Proposed major biosynthesis routes and classification of meliaceous limonoids. B dx.doi.org/10.1021/cr9004023 |Chem. Rev. XXXX, XXX, 000–000 Chemical Reviews REVIEW Table 1. Structures and Sources of Azadirone-Class Limonoids 1À80 no. compounds substitution groups and others sources 57À59,80À83 1 azadirone R1 =R3 =R4 =R5 =H;R2 =Ac Azadirachta indica; Entandrophragma delevoyi;75 Melia toosendan;76,84,85Trichilia havanensis;86Turraea robusta;87 Khaya anthotheca60 88 2 7-deacetoxy-7-hydroxyazadirone R1 =R2 =R3 =R4 =R5 =H Walsura piscidia α 60 3 11 -acetoxyazadirone R1 =R4 =R5 =H;R2 = Ac, Khaya anthotheca α R3 = -OAc β 60,89 4 11 -acetoxyazadirone R1 =R4 =R5 =H;R2 = Ac, K. anthotheca β R3 = -OAc α 90 5 12 -acetoxy-7-deacetylazadirone R1 =R2 =R3 =R5 =H;R4 = OAc Turraesa cornucopia 91 6 chisosiamensin R1 =R3 =R4 =R5 =H; Chisocheton siamensis Δ5,6 R2 = Ac; α 61,62,64,92 7 nimonol (nimocinol) R1 = -OH; R2 = Ac; R3 = Azadirachta indica R4 =R5 =H α α 93 8 6 -O-acetyl-7-deacetylnimocinol R1 = -OAc; R2 =R3 =R4 = A. indica R5 =H α α 69,94À96 9 6 -acetoxyazadirone (paniculatin) R1 = -OAc; R2 = Ac; R3 = Chisocheton paniculatus; 75 R4 =R5 =H Entandrophragma delevoyi 80 10 nimocin R1 =R3 =R4 =R5 =H;R2 =Bz Azadirachta indica β 66 11 dysobinin R1 = -OAc; R2 = Ac; R3 =R4 = Dysoxylum binetariferum; 91,97 R5 =H Chisocheton siamensis 91,97 98 12 azadiradione R1 =R3 =R4 =H;R2 = Ac; R5 =O C. siamensis; Cedrela odorata; Quivisia papinae;99Lansium domesticum;100 À À Azadirachta indica57,58,70,80 82,101 108 101,109,110 13 nimbocinol (7-deacetylazadiradione) R1 =R2 =R3 =R4 =H;R5 =O A. indica 68,70 14 7-desacetyl-7-benzoylazadiradione R1 =R3 =R4 =H;R2 = Bz; R5 =O A. indica (7-benzoylnimbocinol) α α 99 15 7-deacetyl-7-angeloyl-6 -hydroxyazadiradione R1 = -OH; R2 = Ang; R3 = Quivisa papinae R4 =H;R5 =O α α 99 16 6 -hydroxyazadiradione R1 = -OH; R2 = Ac; R3 =R4 =H; Q. papinae R5 =O α α 69 17 6 -acetoxy-16-oxoazadirone (mahonin) R1 = -OAc; R2 = Ac; R3 =R4 =H; Chisocheton paniculatus; 71,111,112 R5 =O Swietenia mahagoni β 113 18 17 -hydroxyazadiradione R1 =H;R2 =Ac Carapa guianensis; À Azadirachta indica70,81,103,104,109,114 116 β 101,107 19 7-deacetyl-17 -hydroxyazadiradione R1 =R2 =H A. indica α β 94,117 20 6 -acetoxy-17 -hydroxyazadiradione R1 = OAc; R2 =Ac Chisocheton paniculatus 70 21 7-benzoyl-17-hydroxynimbocinol R1 =H;R2 =Bz Azadirachta indica 22 15-hydroxyazadiradione A. indica70 23 7-acetyl-16,17-dehydro-16- A. indica70 hydroxyneotrichilenone 118 24 isonimolide R1 = OCH3;R2 = Ac; R3 = A. indica R4 =R5 =H;R6 = OH; R7 =O 118 25 isolimbolide R1 =R5 =H;R2 = Ac; R3 = OAc; A. indica R4 =R6 = OH; R7 =O 80 26 nimocinolide R1 =R7 = OH; R2 = Ac; R3 = A. indica R4 =R5 =H;R6 =O 119 27 23-O-methylnimocinolide R1 = OH; R2 = Ac; R3 =R4 = A. indica R5 =H;R6 =O;R7 = OCH3 α 119,120 28 7-O-deacetyl-23-O-methyl-7 - R1 = OH; R2 = Sen; R3 =R4 =R5 =H; A. indica O-senecioylnimocinolide R6 =O;R7 = OCH3 80,118 29 isonimocinolide R1 =R6 = OH; R2 = Ac; R3 =R4 =R5 =H; A. indica R7 =O C dx.doi.org/10.1021/cr9004023 |Chem. Rev. XXXX, XXX, 000–000 Chemical Reviews REVIEW Table 1. Continued no. compounds substitution groups and others sources 121 30 nimbocinolide R1 =R5 =H;R2 = Ac; R3 = OiBu(OH); A. indica R4 =R7 = OH; R6 =O 122 31 isonimbocinolide R1 =R5 =H;R2 = Ac; R3 = OiBu(OH); A. indica R4 =R6 = OH; R7 =O 92 32 meliacinanhydride R1 = OH; R2 = Ac; R3 = OCH3;R4 = OAc; A. indica R5 =H;R6 =R7 =O 120 33 22,23-dihydronimocinol R1 = OH; R2 = Ac; R3 =R4 =R5 =R6 = A. indica Δ20,21 R7 = H; 22,23-dihydro; 123 34 azadironolide R1 =R3 =R4 =R5 =H;R2 = Ac; R6 =O; A.
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